Hydrochloric Acid → 6-Acrylamidohexanoic Acid

To a solution of 6-Aminocaproic acid (10.0 g) in a 1.27 M aqueous sodium hydroxide solution (60 ml) was added a solution of acryloyl chloride (7.8 ml) in tetrahydrofuran (20 ml) dropwisely while chilling in ice water. During the addition, the reaction mixture was adjusted to be pH 8 to 9 by addition of 4 N aqueous sodium hydroxide solution. After the addition, the resulting mixture was stirred for 2 hours while being gradually cooled to room temperature. Subsequently, the reaction mixture was adjusted to be pH 3 by addition of 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with distilled water and dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and recrystallized from hexane to give the target compound (9.6 g).

1. additionDuring the addition
2. additionAfter the addition
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with distilled water
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe magnesium sulfate was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. dissolutionThe residue was dissolved in a small amount of ethyl acetate
9. customrecrystallized from hexane

ORD record

ord-d4cac2cbf3c64ec9b41c56197ae818f6

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700701B2